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Synthesis 2015; 47(01): 55-64
DOI: 10.1055/s-0034-1379032
DOI: 10.1055/s-0034-1379032
paper
Mild and Selective Deprotection of tert-Butyl(dimethyl)silyl Ethers with Catalytic Amounts of Sodium Tetrachloroaurate(III) Dihydrate
Further Information
Publication History
Received: 04 June 2014
Accepted after revision: 05 August 2014
Publication Date:
15 September 2014 (online)
Abstract
A simple and mild method for the removal of tert-butyl(dimethyl)silyl (TBS) protecting groups with catalytic amounts of sodium tetrachloroaurate(III) dihydrate is described. The procedure permits selective deprotection of aliphatic TBS ethers in good to excellent yields in the presence of aromatic TBS ethers, aliphatic triisopropylsilyl ethers, aliphatic tert-butyl(diphenyl)silyl ethers, or sterically hindered aliphatic TBS ethers. Additionally, TBS ethers can also be transformed into 4-methoxybenzyl ethers or methyl ethers in one pot by using larger quantities of the catalyst and a higher reaction temperature.
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